Yellow mono-azo dyestuff



Patented Sept. 13, 1932 *,fS-TATES "PATENT OFFICE f ,f ,ggmxror-oN-THEMAImHooHSif; GERMANY, .essIvGoRs To GENERAL ANILINE i Y wonxgj'ma, on NEW Yoann. Y.,A"oomgoRA'rIoN oF DELAWARE ,n i

mono-azo dyestuis. fj ,CHS Y *10H3 l 0H: The new dyeetdlshave the following genz 11" Op; ,Hogs-f M eral formula f 'Y Y f i.

H Le 50 ing` chrome leather; A

The hitherto Unknown Q Chlordcol. o

present frelatesfztdgyellow d. `rljhelreaetion takes thedollowing Vcoursei` y The following dimples illustrate our VViii- Ventin; vthe parts being by Weight:y

f "(1) `221.5 partsqf'eichioro@amino-uneth-m a'ustio Soda are 'dissolved in 10;()00'partsof Water."v` 7 O partsloflsodium nitrite 'are V'added nsohitionyisd riin into the IniXtiire the Whole @ma igriiiight yellow powder.'

is subsequently run, While's'tirringQinto agg solution of 110 jp'arts of resoieinol and 100 parts ofoaiit'idsodain 450040 `partsof Water. Stirring is'-oontinued for 2 hours until the coupling is'nished, the solution is heated to 7 OO C., the dyestuif is salted out addingagg mammie-a1effacement ma@ at com@ Sle' filtered lby suction andsdried.

`lThe dyestuif thus obtained has theffoll'owing constitution: Y

. `'leather a .very pureiorangeyel'low tint; As .x30

oonceiitrated ysulfuric i acid Containing '20, vper Stweleida@e@diliitdredfileiieife;d-V

regards the pureness of shade it eqiialethatof the basic phosphine dyestufs.U

'` ,*Thefdyestufis diiiioultly soluble inzaloohol and in glacrialfaoetieaeid, 'inoluble inlbhenzene and chloroform. It dissolves in conceda-B6 trated V$111fiirieaoidtoa reddish-brown solution; Wli'ediliiting'the'iiirideid solution With Waterfa clear golden yellowsolution is of water.

chloro-c-amino -1- methylbenzene -6- sulfonic acid in the manner indicated in eXample 1 is run at 15 C. into a solution of 226 parts of 1.3- dimethoxybenzene -QA- dicarboxylic-acid and 100 parts of caustic soda in 4000 parts The whole is stirred for 2 hours in order to complete the copulation, the solution is heated to C., the coupling product is salted out, filtered and dried. The dyestu thus obtained has the following constitution:

c1 H300 ooon moQ-rhN-Qoom 03H Y Y Coon This dyestuff dyes chrome leather a tint which is a little more yellowish than that.

obtained according to Example 1, but its color is a little less intense; when dried it is-l an orange colored powder. It is difcultly soluble in alcohol and glacial acetic acid, insoluble in benzene and chloroform. It dissolves in concentrated. sulfuric acid to a brownish-yellow solution; when diluting the sulfuric acid solution with water a clear yellow solution is obtained.

(3) The diazo solution obtainable from 2- chloro-l-amino -1- methylbenzene -6- sulfonic acid inthe manner indicated in Example 1 is runat 15 C. into a solution of 160 parts of A1.S-dihydroXynaphthalene and 50 parts of caustic soda in 4000 parts of water. The whole is heated for two hours in order to accomplish the coupling; the solution of the v dyestu is heated to 70 C., the dyestuif is salted out by adding common salt, filtered byv suction and dried.

The dyestuff thus obtained hasthe following constitution:

Cl OH Y :Eno- N--N .on

soin

It dyes chrome leather a yellow tint being j a little more dull than that obtainable from the dyestuif according to Example 1.

When dried the dyestuif is a red brown powder. It is sparingly soluble in alcohol and glacial acetic acid, insoluble in benzene and chloroform. It dissolves in concentrated sulfuric acid to a brownish-red solution;

when diluting the sulfuric acid solution with water the dyestulf slowly separates in brown flakes.

We claim:

1. As new products, mono-azo dyestufl's of the following general formula:

Hoas Y wherein R stands for hydrogen or CH3 and X and Y stand for hydrogen or each for a carboxylic group, being when dried orange to light-brown powders, dyeing chrome leather pure yellow to orange yellow tints, dissolving in concentrated sulfuric acid to a brownish-yellow to reddishyellow solution and being diliicultly soluble in alcohol and glacial acetic acid.

2. As a new product, the mono-azo dyestuff of the following formula:

Cl HO Y HOQS leather yellow to orange-yellow tints, dissolve.

ing in concentrated sulfuric acid to abrownish-yellow to reddish-yellow solution and being diicultly soluble in alcohol and' glacial acetic acid. f

4. As new products, mono-azo dye-stuffs of the following general formula:

Y 1 wherein R stands for hydrogen or alkyl and Y1l stands for hydrogen or for a carboxylic. group, being in the dry state orange to reddish-brown powders, dyeing chrome leather` yellow to orange-yellowtints, dissolving in concentrated sulfuric acid to a brownishyellow to reddish-yellow solution and being dif'lcultly soluble in alcohol and glacial acetic aci Y H .f

stuff of the following formula:

being in the dry `state an orange powder, dyeing chrome leather an orange-yellow'tint and dissolving in concentrated sulfuric acid to a brownish-yellow solution whichv on dilution with water turns clear` yellow.

In testimony whereof, we affix our signatures. "f

HERMANN waGNER. BARTHoLoMAUs vossEN.

' .115 5. As a new product, the mono-azo dye- 

